Wax-like esters and method of preparing the same



' Patented Aug. 29,1933

WAX-LIKE ESTERS il METHOD Donald K. Tressler, Pittsburgh, rs, gator toThe Mathieson N. 2., a corporation oi Works,

limo New York,

No Drawing. Application December 4, is- -Serial No. dllflidt Thisinvention relates to new wax-like products and toa'new methodofpreparing the same.

The new wax -like products are condensation products'of chlorhydrins ofunsaturated fats, fettyacid esters, fatty acid ketones, or fatty acidswith soaps. I have found that the chlorhydrins of the fatty acids,.fatty acid esters, and fatty acid ketones, including the simple estersand glycerides, .form new and valuable wax-like products by fusion withsoaps of the alkali or alkaline earth metals.- The new. wax-likeproducts vary from viscous liquid waxes to soft and even hard waxes oivary omomhonzon. ona)1ooon+noci This chlorfrzydrin readilygives up waterto foim an ester with a, lactone linkage as indicated by the followingequation:

When this lactone-like compound is fused with a soap it is convertedinto an ester as illustrated graphically by the following equation:

OHIKGHQIG HABKOH MGOOH cowmnoncnomomncm 011,0cowmncnononbucmtcmmooowmtcnomoncl on,)1cm+scm(oflemcoONE- mocowm ouos.onouosmom,

In a companion application, Set-lei Number 411,699 filed of even datewhich has matured into Patent No. 1,873,072, I have described newchlorhydrins of unsaturated fatty acid ketones which can be'made bytreating the unsaturated fatty acid ketones-with a cold solution ofhypochlorous acid. These new chiorhydrins and those of fatty acid esterscan similarly be condensed with soaps of the alkali and alkaline earthmetals to form new wax-like condensation products or esters. Thecondensation of trichlorhydrin of olein with sodium stearate isillustrated graphically by the following equation.

O-CO(CH5)10UEI5 omocowm) ouomomcmimm 0OO(OHs)|cOHs H000 qlmbononemommmaw-communes (Juiceowntmcnontmommm The cliloi hy'diin oi ethyl cl reactwith sodium stearate es following equation:

omwmhouolonomoem 7J1 mllerly seect omwsmsonoioeouwsrm with sodiumstearste in the giregiofctiens of l? parts of using c. ccnd-cnscz". ingfor noon-t nor. too inaction product was allowed to coci then extractedwith 2,53% ii porn; of ncti'oicuxn her. This coi /ant cxtrnctcd the on ngircduct "while leaving the an ncici'vniuc of :id was with iigypcuticnto viscous onion iii; oer of chlorine. so ports of um: f n-cocci. werccoated with co parts of sodium at i??? C. for co hours. After.

cooling the cstciresulting from the ccndcnsot-Ionwas cxtrcctcd withpctroicum other, Zthc other distilled from the extract, and the residueallowed to of cnlcrnydrin of d with cc ports of sodium ctiiyi ciccctonintc nouns. lilo product was then condensation product ontmctcd 1other. "Upon distilling n the cntrcct inc crude conduct woo obtained csa.

ester or cocoon of ciccnc cisiornydrin cociinatnc 2m iocmcd extractedwith sotrotion of the petroleum icon: cthcr obtcincd.

In gcncmi the esters produccd from unsaturotcd fatty siinnic esters bycondensation with soap rc more or icsc viscous liquid waxes; 'wiiiic t'n by condcns'mg the onion with soaps arc wanes oi oi Such wcxcc arecuiizoucpurpcscs. such on the .cionc, the wntcrpz'coiing cu, for otherpurposes.

'""u2 Icy the condensation oi the free fatty acids .1 inctonc iinkng cnrc acidic duccd c cc icncction oi tho chiozc i cisrccridcc o c aresolid waxes. This are dc= 1 It commercial fatty acids w wc commercialgiyccridcc are W oi dificrcnt acids or ciyc idea. (3.. cin'i a, ccid orred oil, for ct-mmnin, 3165 o i than 'o'icic acid, cc iinoicicccid,zrtccric acid, ctc. Iii-c ciaicrhydrins formcd from ouch fatty ncidc oroiyccridcc wouid cccoiy no mixed ciflorhydx'ms the Won-lino roductc r'duccd condemnation of tin; claim" with com sixniicrig be mixed pccouctcdo iccaoco ofiuzn ctcorutc about ct ports of c. scft't wan were, I

' of a. higher fatty acid; soap with the chlorhydrin contouring otherfatty cc r": upon the cridcs employed.

I cicim: 1. As a new product of as higher fatty acid soap withthechlorhydrin of an unsaturated fatty acid. 1 q

2. As a new product the condensation product of an unsaturated fattyacid ester.

3. no a new product the condensation productof a. higher fatty acid soapwith the chlorhydrin of an unsaturated ictty'ccid giyccriiie.

4. its a new product the condenmtion product of a higheriatty acid soapwith the chlorhydrin of an unsaturated fatty acid ketone.

5. As a new product the waxlike product obtninoblc by the condensationof a higher fatty ncrticular fatty acids or giccthe condensation productof c Znghcr iottyccid soap with the chlorhgdrin acid soap with thechlorhydrin oi on uncaturcted highcr fatty acid giyccride.

6. As a new product the condensation product of a higher fatty acid soapwith the chlorhydrin oi .cn unsaturated fatty acid esters having alactonc linkage. i

7. As a new product the compound-having the formula.

n cnon. on. B1

wncrc R1 and n: are aikyi grou s and R is a di- '1yccridc,'fctty acidcstcror'fc by acid ketone' radical.

8. m a new product the compound having the formin B. cuon. on. B1

where R and Rncre nikyl groups and R1 is a. fatty acid cstcr radicalhaving a lactone linkage. 9. no a. new product the condensation productof. compound from the group of compounds consisting of unsaturated fattyacids, unsaturated ond unsaturated fatty acid or the alkali or alkalineearth metals.

hydrin of an unsaturated fatty acid with a soap 11 The method ofproducing new wax-like products, which comprises condensing cchlprnydrinof an unsaturated fatty acid ester with 'c; soup of the alkali oralkaline earth metals.

12. The method of producing new wax-like products, which comprisescondensing the chlorhydrin of unsaturated fctty acid kctone with a scanof the alkali or w earth metals.

13. Tnc method of producing new wax-like products, which comprisescondensing 511th a. song ofthc alkali or alkaline earth metals 2.compound from the group of compounds consist ingci tho cmorhydrins ofunsaturated fatty acids, fatty acid %ters, and fatty acid ketones.

id. method of producing new wax-like prcductc, which comprisescondcnsing the chiorhydrin of an .fatty acid ester having a lccbone 1:with a soap of the alkali .01-

